Part of the Kentucky Downs mystique is its long-ago history of gun duels. Cursory research of the track invariably yields a mention of various gun duels being staged on its spacious property, including those reportedly involving Andrew Jackson, Sam Houston, and other prominent 19th century figures on what then was known as the Sanford Duncan farm. It was in that spirit that Kentucky Downs was founded in 1990 as a steeplechase course known as Dueling Grounds, with a name change coming in 1997 following a turbulent period for the original owners. Fast forward a quarter-century, and the top stakes restricted to 3-year-olds every September at Kentucky Downs stand as living memorials to that curious past. The $500,000 Dueling Grounds Oaks and $750,000 Dueling Grounds Derby are those back-to-back co-features Monday after Sunday's card was rescheduled due to rain at the turf-only track straddling the border of Kentucky (where dueling was legal in the early 1800s) and Tennessee (where it wasn’t). Both will be run at the once-around distance of 1 5/16 miles over the undulating course. Both races drew oversubscribed and highly competitive fields with also-eligible lists (only as many as 12 can start), and both drew top contenders from the Brad Cox stable, those being Turnerloose in the Oaks and Ready to Purrform in the Derby. :: Bet the races with a $200 First Deposit Match and FREE Formulator PPs! Join DRF Bets. First post for an 11-race Monday card is 12:25 p.m. Central, with the Oaks going as race 9 (4:57) and the Derby as race 10 (5:31). Half the purse for both stakes comes from the Kentucky Thoroughbred Development Fund, with the English-bred filly Skims (Oaks) being the only ineligible runner in either race. After Monday, the third of seven programs at this boutique meet, live action at Kentucky Downs resumes Thursday, with the final three dates being Sept. 10, 11, and 14. Dueling Grounds Oaks Even when earning a Beyer Speed Figure of just 71, Turnerloose was one of the more visually impressive winners at the 2021 meet when gliding to a five-length score in the Juvenile Fillies. “She got over the ground really well there last year,” Cox said from his Churchill Downs base. “We’re excited about getting her back down there.” A year later, Turnerloose is now a Grade 2 winner on dirt, having won the Rachel Alexandra at Fair Grounds in February with an 81 Beyer – but her best efforts might still be ahead as Cox said he intends to keep running her on the grass in the immediate future. Turnerloose, with Florent Geroux riding from post 10, figures to vie for favoritism with New Year’s Eve – who, for her part, also was an eye-catching winner of the Grade 2 Edgewood on Kentucky Derby weekend at Churchill. Brendan Walsh is the trainer of New Year’s Eve (post 7, Tyler Gaffalione). Other possibilities include Skims (post 12, Julien Leparoux), in from Saratoga for Shug McGaughey, and Vergara (post 5, Joel Rosario), a handy type in from Fair Hill for Graham Motion. A handful of viable longer-priced plays includes California Angel (post 11, DeShawn Parker), best known for her upset of the Grade 2 Jessamine last fall at Keeneland, and Silverleaf (post 4, Brian Hernandez Jr.), a Speightster filly making her grass debut for Kenny McPeek. This is the eighth Dueling Grounds Oaks. McPeek has won it twice, with Daddys Lil Darling (2017) and Princesa Carolina (2019). Cox won it for the first time last year with Adventuring, an 11-10 favorite. Dueling Grounds Derby Ready to Purrform dominated the Grade 2 Hall of Fame going a mile on the Saratoga turf, with Rosario giving the versatile colt a cagey front-running ride. Cox is looking for a similar result 30 days later. “I like the fact he’ll be going a little farther,” Cox said. “We’ve thought he could be a mile and an eighth, mile and a quarter kind of horse – so the mile and five-sixteenths should really suit him. We hadn’t seen the type of speed he showed last out before, but obviously it worked out well. He came out of it in great shape and hopefully he’s in another good spot.” Rosario will be back aboard when Ready to Purrform leaves from post 12. The main challengers could be Grand Sonata (post 1, Gaffalione), a two-time stakes winner exiting back-to-back Grade 1 turf races in New York for Todd Pletcher, or Double Clutch (post 6, Geroux), who gave closest chase to Ready to Purrform for much of the Hall of Fame before fading to fifth. A multitude of fringe players include Running Bee (post 7, Vince Cheminaud), a last-out maiden winner at Saratoga for Chad Brown, and the uncoupled Michelle Nihei duo of Always Above (post 3, Joe Talamo) and Mount Rundle (post 5, Rafael Bejarano). This is the ninth running of the Dueling Grounds Derby. Pletcher has won it twice, with Channel Cat (2018) and Social Paranoia (2019). Accredit, a 36-1 shot, won it last year for trainer Pavel Matejka.